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Pure Appl. Chem., 1985, Vol. 57, No. 12, pp. 1855-1864

http://dx.doi.org/10.1351/pac198557121855

Recent advances in arene transformation reactions via chromium complexes

E. P. Kündig

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  • Bădoiu Andrei, Kündig E. Peter: Electronic effects in 1,3-dipolar cycloaddition reactions of N-alkyl and N-benzyl nitrones with dipolarophiles. Biomol Chem 2012, 10, 114. <http://dx.doi.org/10.1039/c1ob06144e>
  • Arrais Aldo, Diana Eliano, Marabello Domenica, Gervasio Giuliana, Stanghellini Pier Luigi: Syntheses of chromium tricarbonyl organometals of 1-methyl-naphthalene and different polycyclic aromatic hydrocarbons, characterisation of the (C11H10)Cr(CO)3 isomers and the crystal structure of the [(η6-5,6,7,8,9,10-C11H10)Cr(CO)3] complex. J Organomet Chem 2011, 696, 2299. <http://dx.doi.org/10.1016/j.jorganchem.2010.12.005>
  • Astruc Didier, Ruiz Jaime: Organo-iron mediated synthesis of functional dendrimers with 1 → 3 connectivity. J Organomet Chem 2011, 696, 2864. <http://dx.doi.org/10.1016/j.jorganchem.2011.03.011>
  • Mercier Audrey, Urbaneja Xavier, Yeo Wee Chuan, Chaudhuri Piyali Datta, Cumming Graham R., House David, Bernardinelli Gérald, Kündig E. Peter: Asymmetric Catalytic Hydrogenolysis of ArylHalide Bonds in Fused Arene Chromium and Ruthenium Complexes. Chem Eur J 2010, 16, 6285. <http://dx.doi.org/10.1002/chem.201000011>
  • Habib Osama Mahmoud Ali, Zhao-Karger Zhirong, Abdelhamid Ismail Abdelshafy, Wartchow Rudolf, Butenschön Holger: Phthalimide Tricarbonylchromium Complexes: Synthesis, Characterization, Nucleophilic Addition, and Unanticipated syn Adduct Formation upon Addition of Propynyllithium. Eur J Org Chem 2010, 2010, 6072. <http://dx.doi.org/10.1002/ejoc.201000758>
  • Aminocarben-Komplexe. Nachr Chem Tech Lab 2010, 38, 872. <http://dx.doi.org/10.1002/nadc.19900380711>
  • Astruc Didier, Ruiz Jaime: Organoiron-mediated dendrimer syntheses with 1→3 connectivity and applications. Tetrahedron 2010, 66, 1769. <http://dx.doi.org/10.1016/j.tet.2009.11.116>
  • Muschalek Bianka, Weidner Ingo, Butenschön Holger: Synthesis of tricarbonyl(N-methylisatin)chromium(0) and an unanticipated transformation of a N-MEM to a N-MOM group. J Organomet Chem 2007, 692, 2415. <http://dx.doi.org/10.1016/j.jorganchem.2007.02.034>
  • Oh Moonhyun, Reingold Jeffrey A., Carpenter Gene B., Sweigart Dwight A.: Manganese tricarbonyl transfer (MTT) reagents in the construction of novel organometallic systems. Coord Chem Rev - 2004, 248, 561. <http://dx.doi.org/10.1016/j.ccr.2003.12.002>
  • Rose-Munch Françoise, Rose Eric: cine andtele Nucleophilic Substitutions in (η6-Arene)tricarbonylchromium and Tricarbonyl(η5-cyclohexadienyl)manganese Complexes. Eur J Inorg Chem 2002, 2002, 1269. <http://dx.doi.org/10.1002/1099-0682(200206)2002:6<1269::AID-EJIC1269>3.0.CO;2-9>
  • MUKAI Chisato: Development of Highly Selective Reactions Based on Metal Carbonyls and Its Application to Synthesis of Bioactive Compounds. YAKUGAKU ZASSHI 2002, 122, 889. <http://dx.doi.org/10.1248/yakushi.122.889>
  • Rudler Henri, Comte Virginie, Garrier Eva, Bellassoued Moncef, Chelain Evelyne, Vaissermann Jacqueline: Meta, para and meta, ortho double exo nucleophilic additions of trimethylsilylester enolates derived from saturated and unsaturated carboxylic acids to tricarbonylchromium complexes of aryl ethers: dearomatizing cyclization to lactones. J Organomet Chem 2001, 621, 284. <http://dx.doi.org/10.1016/S0022-328X(00)00848-2>
  • Abd-El-Aziz Alaa S., Bernardin Shelly: Synthesis and reactivity of arenes coordinated to cyclopentadienyliron cations. Coord Chem Rev - 2000, 203, 219. <http://dx.doi.org/10.1016/S0010-8545(99)00182-4>
  • Pike Robert D., Sweigart Dwight A.: Electrophilic reactivity of coordinated cyclic π-hydrocarbons. Coord Chem Rev - 1999, 187, 183. <http://dx.doi.org/10.1016/S0010-8545(98)00231-8>
  • Gopal Dongol Krishna, Krüger Jörn, Schnebel Matthias, Voigt Beate, Wartchow Rudolf, Butenschön Holger: Tricarbonylchromium complexes with methoxy substituted benzocyclobutenone and benzocyclobutenedione ligands. Inorg Chim Ada 1999, 296, 150. <http://dx.doi.org/10.1016/S0020-1693(99)00353-9>
  • Voigt Beate, Brands Michael, Goddard Richard, Wartchow Rudolf, Butenschön Holger: Addition and Ring Expansion Reactions of Tricarbonyl(1,2-dioxobenzocyclobutene)chromium(0) with Carbon Nucleophiles – Unexpected Formation of Benzocycloheptene Derivatives and the First Head-to-Head Coupling of Two Methoxyallene Molecules. Eur J Org Chem 1998, 1998, 2719. <http://dx.doi.org/10.1002/(SICI)1099-0690(199812)1998:12<2719::AID-EJOC2719>3.0.CO;2-H>
  • Rose-Munch Françoise, Gagliardini Vanessa, Renard Christophe, Rose Eric: (η6-Arene)tricarbonylchromium and (η5-cyclohexadienyl) tricarbonylmanganese complexes: indirect nucleophilic substitutions. Coord Chem Rev - 1998, 178-180, 249. <http://dx.doi.org/10.1016/S0010-8545(98)00078-2>
  • Gagliardini Vanessa, Onnikian Valérie, Rose-Munch Françoise, Rose Eric: Chromium hydride intermediates in the case of cine and tele-meta nucleophilic aromatic substitution on arenetricarbonylchromium complexes. Inorg Chim Ada 1997, 259, 265. <http://dx.doi.org/10.1016/S0020-1693(97)05452-2>
  • Brands Michael, Wey Hans G., Krömer Rainer, Krüger Carl, Butenschön Holger: η6-(1-oxobenzocyclobutene)tricarbonylchromium(0): Preparation, reduction, and ring-opening/cycloaddition chemistry of the 1-hydroxybenzocyclobutene complex. Liebigs Ann /Recueil 1995, 1995, 253. <http://dx.doi.org/10.1002/jlac.199519950235>
  • Huang Ting-Yu, Chen Chi-Tain, Gau Han-Mou: The synthesis, characterizations and structures of Group 4 metal-chromium complexes bridged by an OC6H4CH3 group. J Organomet Chem 1995, 489, 63. <http://dx.doi.org/10.1016/0022-328X(94)05158-8>
  • Kyoungja Woo, Carpenter G.B., Sweigart D.A.: The synthesis and reactions of A-ring aromatic steroid complexes of manganese tricarbonyl. Inorg Chim Ada 1994, 220, 297. <http://dx.doi.org/10.1016/0020-1693(94)03882-1>
  • Uemura Motokazu, Nishimura Hikaru, Kamikawa Ken, Shiro Motoo: Synthesis and structure of Cr(CO)3 complexes of biphenyl compounds with axial chirality. Inorg Chim Ada 1994, 222, 63. <http://dx.doi.org/10.1016/0020-1693(94)03894-5>
  • Rose-Munch Françoise, Khourzom Rami, Djukic Jean-Pierre, Perrotey Anne, Rose Eric, Brocard Jacques: Réactivité d'halogénobenzène tricarbonylchrome vis-à-vis d'anions de sulfones. J Organomet Chem 1994, 467, 195. <http://dx.doi.org/10.1016/0022-328X(94)80006-5>
  • Moulines Francoise, Djakovitch Laurent, Boese Roland, Gloaguen Bruno, Thiel Werner, Fillaut Jean-Luc, Delville Marie-Hélène, Astruc Didier: Metallorganische molekulare Bäume als Mehrelektronen- und Mehrprotonenspeicher: CpFe+-induzierte Nonaallylierung von Mesitylen und phasentransferkatalysierte Synthese eines redoxaktiven Nonaeisenkomplexes. Angew Chem 1993, 105, 1132. <http://dx.doi.org/10.1002/ange.19931050740>
  • Moulines Françoise, Djakovitch Laurent, Gloaguen Bruno, Thiel Werner, Fillaut Jean-Luc, Delville Marie-Hélène, Astruc Didier, Boese Roland: Organometallic Molecular Trees as Multielectron and Multiproton Reservoirs: CpFe+-Induced Nonaallylation of Mesitylene and Phase-Transfer Catalyzed Synthesis of a Redox-Active Nonairon Complex. Angew Chem Int Ed Engl 1993, 32, 1075. <http://dx.doi.org/10.1002/anie.199310751>
  • Angermund Klaus P., Betz Peter, Butenschön Holger: (Bicyclo[3.2.0]hepta-1,3-dienyl)cobalt(I) Complexes. Chem Ber 1993, 126, 713. <http://dx.doi.org/10.1002/cber.19931260323>
  • Lee T.-Y., Kang Y.K., Chung Y.K., Pike R.D., Sweigart D.A.: Manganese-mediated synthesis of cis-disubstituted cyclohexadienes via double nucleophilic addition to coordinated arenes. Inorg Chim Ada 1993, 214, 125. <http://dx.doi.org/10.1016/S0020-1693(00)87533-7>
  • Semmelhack M.F., Rhee Hakjune: Formal synthesis of teleocidin a via indole-Cr(CO)3 complexes. Tetrahetron Lett 1993, 34, 1399. <http://dx.doi.org/10.1016/S0040-4039(00)60301-5>
  • Kändig Ernst Peter, Ripa Alberto, Bernardinelli Gérald: Diastereoselektive Synthese substituierter Cyclohexadiene aus enantiomerenreinen Tricarbonyl(2-phenyl-4,5-dihydrooxazol)chrom-Komplexen. Angew Chem 1992, 104, 1115. <http://dx.doi.org/10.1002/ange.19921040849>
  • Kündig Ernst Peter, Ripa Alberto, Bernardinelli Gérald: Diastereoselective Synthesis of Substituted Cyclohexadienes from Enantiomerically Pure Tricarbonyl(2-pheny1-4, 5-dihydrooxazole)chromium Complexes. Angew Chem Int Ed Engl 1992, 31, 1071. <http://dx.doi.org/10.1002/anie.199210711>
  • Weber Jacques, Morgantini Pierre-Yves, Eisenstein Odile, Meghezzi H., Boucekkine A., Silla E., Tu����n I., Villar F., Pascual-Ahuir J.L.: Molecular graphics investigation of the addition of nucleophiles to (��4-butadiene) M(CO)3 complexes (M = Fe, Co+). Journal of Molecular Structure: THEOCHEM 1992, 254, 343. <http://dx.doi.org/10.1016/0166-1280(92)80079-2>
  • Stussi Dominique, Weber Jacques, Fluekiger Peter, Morgantini Pierre-Yves, Kündig E. Peter: Development and Applications of an Extended-üuckel-Based Reactivity Index for Organometallic Complexes. Comments Inorg Chem 1992, 14, 27. <http://dx.doi.org/10.1080/02603599208048656>
  • Wey Hans G., Betz Peter, Butensch ön Holger: Synthesis, Characterization, and Some Reactions of Tricarbonyl(cyclobutabenzene)chromium(O) Derivatives. Chem Ber 1991, 124, 465. <http://dx.doi.org/10.1002/cber.19911240308>
  • Kündig E. Peter, Grivet Chantal, Wenger Eric, Bérnardinelli Gerald, Williams Alan F.: Addition of Carbon Nucleophiles to Tricarbonylchromium Complexes of 1,2-Dihydrocyclobutabenzene, Indane, 1,2,3,4-Tetrahydronaphtbalene andortho-Xylene. HCA 1991, 74, 2009. <http://dx.doi.org/10.1002/hlca.19910740836>
  • Rose-Munch Françoise, Aniss Khadija, Rose Eric, Vaisserman Jacqueline: Synthèse et étude conformationnelle de complexes obtenus par action d'anions d'α-iminoesters ou nitriles sur des halogénobenzènetricarbonylchrome. J Organomet Chem 1991, 415, 223. <http://dx.doi.org/10.1016/0022-328X(91)80122-Z>
  • Sutherland Ronald G., Zhang Chunhao, Piórko Adam: Cyclopentadienyliron-mediated introduction of functionalized alkyl or alkynyl groups to arenes in an addition—demetallation sequence. J Organomet Chem 1991, 419, 357. <http://dx.doi.org/10.1016/0022-328X(91)80248-I>
  • Uemura Motokazu, Minami Tatsuya, Shinoda Yoshio, Nishimura Hikaru, Shiro Motoo, Hayashi Yuji: Regioselectivity of nucleophilic additions to (arene) chromium complexes: conformational effects of Cr(CO)3 moieties and the nature of carbanions. J Organomet Chem 1991, 406, 371. <http://dx.doi.org/10.1016/0022-328X(91)83125-N>
  • Rose-Munch Françoise, Mignon Laurent, Souchez Jean Paul: Double nucleophilic addition to fluoroarenetricarbonylchromium complexes. Tetrahetron Lett 1991, 32, 6323. <http://dx.doi.org/10.1016/0040-4039(91)80158-3>
  • Mukai Chisato, Cho Won Jea, Kim In Jong, Kido Masaru, Hanaoka Miyoji: Asymmetric aldol reaction: A highly -selective aldol reaction between tricarbonyl(-trimethylsilylbenzaldehyde derivative )-chromium (0) complexes and cyclic silyl enol ethers. Tetrahedron 1991, 47, 3007. <http://dx.doi.org/10.1016/S0040-4020(01)96032-6>
  • Kündig Ernst Peter, Bernardinelli Gérald, Leresche James, Romanens Patrick: Intramolekulare Umwandlung vonsyn- undanti- Tricarbonyl(1-ethoxy-1,2-dihydrocyclobutabenzol)chrom; Abfangreaktion desortho-Chinodimethan-Intermediats. Angew Chem 1990, 102, 421. <http://dx.doi.org/10.1002/ange.19901020419>
  • Kündig E. Peter, Cunningham Allan F., Paglia Patrick, Simmons Dana P., Bernardinelli Gérald: trans-Disubstituted Cyclohexadienesvia Sequential Addition of a Carbon Nucleophile and an Electrophile to (η6-Benzene)tricarbonylchromium: Scope of Carbon Electrophiles. HCA 1990, 73, 386. <http://dx.doi.org/10.1002/hlca.19900730218>
  • Kündig E. Peter, Ferret Celia, Rudolph Bruno: Bicyclo[4.2.0]octa-1,3,5-triene: 2-Mono- and 2,5-Disubstituted Derivativesvia Highly Regioselective Lithiation of Its Cr(CO)3 Complex andvia Reductive Silylation/Oxidation. HCA 1990, 73, 1970. <http://dx.doi.org/10.1002/hlca.19900730720>
  • Daul Claude, Goursot Annick, Morgantini Pierre-Yves, Weber Jacques: The modeling of nucleophilic and electrophilic additions and substitutions using extended Hückel-based reaction potentials. Int J Quantum Chem 1990, 38, 623. <http://dx.doi.org/10.1002/qua.560380505>
  • Ohlsson Bengt, Ullenius Christina, Jagner Susan, Grivet Chantal, Wenger Eric, Kündig E.Peter: Indanetricarbonylchromium: the effects of 1-syn- and 1-anti substituents on the regioselectivity of nucleophilic addition. Crystal structures of 1-syn- and 1-anti- methoxyindanetricarbonylchromium. J Organomet Chem 1989, 365, 243. <http://dx.doi.org/10.1016/0022-328X(89)87025-1>
  • Rose-Munch Françoise, Rose Eric, Semra Assia, Mignon Laurent, Garcia-Oricain Jésus, Knobler Caroline: Substitutions nucléophiles aromatiques SNAr de fluorobenzènetricarbonylchrome. J Organomet Chem 1989, 363, 297. <http://dx.doi.org/10.1016/0022-328X(89)87117-7>
  • Jaouen Gerard, Howell James A.S., Tirvengadum Marie-Claire, McArdle Patrick, Cunningham Desmond: Diastereoisomer separation and absolute configuration of (ortho- and (meta-MeC6H4CO2Me)Cr(CO)2L (L = (+)-neomenthyl-PPh2). J Organomet Chem 1989, 370, 51. <http://dx.doi.org/10.1016/0022-328X(89)87274-2>
  • Rose-Munch Françoise, Rose Eric, Semra Assia, Bois Claudette: Substitutions nucléophiles aromatiques SNAr cine et télé sur lortho, le méta et le para-chlorotoluènetricarbonylchrome. J Organomet Chem 1989, 363, 103. <http://dx.doi.org/10.1016/0022-328X(89)88044-1>
  • Kuhn Norbert, Schumann Hans, Winter Manfred, Zauder Edgar: Synthese und Reaktivität von Dienylmetall-Verbindungen, XXIX. Pretonierung von C5H5FeC6H7 zu Cyclohexadien und Folgereaktionen. Chem Ber 1988, 121, 111. <http://dx.doi.org/10.1002/cber.19881210117>
  • Hegedus Louis S.: Transition metals in organic synthesis annual survey covering the year 1986. J Organomet Chem 1988, 343, 147. <http://dx.doi.org/10.1016/0022-328X(88)80176-1>
  • Rockett Bernard W., Marr George: Selected reactions of transition metal π-complexes annual survey covering the year 1986. J Organomet Chem 1988, 343, 553. <http://dx.doi.org/10.1016/0022-328X(88)80178-5>
  • Rose-Munch Françoise, Rose Eric, Semra Assia, Jeannin Yves, Robert Francis: Substitution nucleophile aromatique cine en serie arenetricarbonylchrome. J Organomet Chem 1988, 353, 53. <http://dx.doi.org/10.1016/0022-328X(88)80299-7>
  • Ohlsson Bengt, Ullenius Christina: Reversible addition of carbon nucleophiles to some nitrogen-substituted η6-arenetricarbonylchromium(0) compounds. J Organomet Chem 1988, 350, 35. <http://dx.doi.org/10.1016/0022-328X(88)80359-0>
  • Cambie Richard C., Clark George R., Gallagher Stewart R., Rutledge Peter S., Stone Martin J., Woodgate Paul D.: Chemistry of the podocarpaceae. J Organomet Chem 1988, 342, 315. <http://dx.doi.org/10.1016/0022-328X(88)83005-5>
  • Meyers A.I., Lutomski Kathryn A., Laucher Dominique: Regio- and stereoselective addition of organolithiums to naphthalenes. an efficient synthesis of 11,2-trisubstituted and trans-2-disubstituted dihydronaphthalenes. Tetrahedron 1988, 44, 3107. <http://dx.doi.org/10.1016/S0040-4020(01)85942-1>
  • Meyers A.I., Brown Jack D., Laucher Dominique: Stereospecific conjugate addition of organolithium reagents to naphthylimines. A facile route to 1,1,2- and 1,2-substituted dihydroronaphthalenes. Tetrahetron Lett 1987, 28, 5279. <http://dx.doi.org/10.1016/S0040-4039(00)96707-8>